Efficient room temperature copper(I) mediated 5-endo radical cyclisations

Tetrahedron Letters

Volumn 40, Issue 49, 1999, Pages 8619-8623

  Clark, Andrew J ^a   Dell, Colin P ^b   Ellard, John M ^a   Hunt, Nicola A ^a   McDonagh, John P ^a  

^a UNIVERSITY OF WARWICK   (United Kingdom)

^b ELI LILLY AND COMPANY   (United States)

Author keywords

Copper; Copper compounds; Cyclisations; Enamides; Radical reactions; Radicals

Indexed keywords

2 PYRROLIDONE DERIVATIVE; AMIDE; BETA LACTAM; BROMINE; COPPER; COPPER DERIVATIVE; RADICAL;

ARTICLE; CATALYST; CHEMICAL MODIFICATION; CYCLIZATION; OXIDATION; REACTION ANALYSIS; REDUCTION; TEMPERATURE;

EID: 0033521154     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01806-7     Document Type: Article

References (24)

1. Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519-564.
2. (a) Udding, J. H.; Tuijp, K. C. J. M.; Vanzanden, M. N. A.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1994, 59, 1993.
3. (b) Udding, J. H.; Tuijp, K. C. J. M.; Vanzanden, M. N. A.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1994, 50, 1907.
4. (c) Baldovini, N.; Bertrand, M.-P.; Carrière, A.; Nougier, R.; Plancher, J.-M. J. Org. Chem. 1996, 61, 3205.
5. (d) Nagashima, H.; Ozaki, N.; Ishii, M.; Seki, K.; Washiyama, M.; Itoh, K. J. Org. Chem. 1993, 58, 464.
6. (e) Iwamatsu, S.-i.; Kondo, H.; Matsubara, K.; Nagashima, H. Tetrahedron 1999, 55, 1687.
7. (a) Forti, L.; Ghelfi, F.; Pagnoni, U. M. Tetrahedron Lett. 1996, 37, 2077.
8. (b) Forti, L.; Ghelfi, F.; Libertini, F. E.; Pagnoni, U. M.; Soragni, E. Tetrahedron 1997, 53, 17761.
9. (c) Ghelfi, F.; Bellesia, F.; Forti, L.; Ghirardini, G.; Grandi, R.; Libertini, E.; Montemaggi, M. C.; Pagnoni, U. M.; Pinetti, A.; DeBuyck, L.; Parsons, A. F. Tetrahedron 1999, 55, 1687.
10. (a) Pirrung, F. O. H.; Steeman, W. J. M.; Hiemstra, H.; Speckamp, W. N.; Kaptein, B.; Boeston, W. H. J.; Schoemaker, H. E.; Kamphius, J. Tetrahedron Lett. 1992, 33, 5141.
11. (b) Pirrung, F. O. H.; Hiemstra, H.; Speckamp, W. N.; Kaptein, B.; Schoemaker, H. E. Tetrahedron 1994, 50, 12415.
12. De Campo, F.; Lastécouères, D.; Verlhac, J.-B. Chem. Commun. 1998, 2117.
13. (a) Goodhall, K.; Parsons, A. F.; Tetrahedron 1996, 52, 6739.
14. (b) Sato, T.; Nakumura, N.; Ikeda, K.; Okada, M.; Ishibashi, H.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 1992, 2399.
15. (c) Ishibashi, H.; Higuchi, M.; Ohba, M.; Ikeda, M. Tetrahedron Lett. 1998, 39, 75.
16. (d) Baker, S. R.; Burton, K. I.; Parsons, A. F.; Pons, J. F.; Wilson, M. J. J. Chem. Soc., Perkin Trans. 1 1999, 427.
17. (a) Cassayre, J.; Quiclet-Sire, B.; Saunier, J.-B.; Zard, S. Z. Tetrahedron 1998, 54, 1029.
18. (b) Cassayre, J.; Zard, S. Z. Synlett 1999, 501.
19. (a) Clark, A. J.; Duncalf, D. J.; Filik, R. P.; Haddleton, D. M.; Thomas, G. H.; Wongtap, H. Tetrahedron Lett. 1999, 40, 3807.
20. (b) Clark, A. J.; Filik, R. P.; Thomas, G. H. Tetrahedron Lett. 1999, 40, 4885.
21. All new compounds exhibited satisfactory spectroscopic and analytical data.
22. A typical experimental procedure is as follows. To the substrate (0.3 mmol) in dichloromethane (2.5 ml) at room temperature under nitrogen was added tris-[2-(dimethylamino)ethyl]amine (0.09 mmol) and CuBr (0.09 mmol). The mixture was stirred at room temperature for 20 min and the crude mixture was filtered through silica and evaporated to dryness.
23. Davies, D. T.; Kapura, N.; Parsons, A. F. Tetrahedron Lett. 1999, 40, 8615, previous paper.
24. Ikeda, M.; Ohtani, S.; Sato, T.; Ishibashi, H. Synthesis 1998, 1806.